Mine is different
Stand by for detailed pics.
Thanks. That blank other side helps confirm my hunch about mine being a souvenir from the 1934 World's Fair.
I have a tattered but still readable original cardboard box for it.
That is fantastic! It's interesting that it reads, "Jack in a Box." The period ads terminology is "Jack-in-the-Box." Odder still, Templeton Kenly trademarked that exact phrasing ("Jack-in-the-Box") in 1973 and claimed first use in... wait for it... 1972!
We know better (by your box - and reams of period ads from the late 1920's and 1930's) than their own front office that they were using it long before 1972.
I guess these little guys have been around quite a while.
My research has turned up ads in numerous trade mags between 1927 and 1935. I cannot find any earlier or later, but it wouldn't surprise me if the production outstripped the ads on the later end. It sure looks to me like they introduced it in 1927 and then made a big splash out of them at the World's Fair in their home city and on their 50th anniversary in 1934, and were still making them at least as late as 1935. But again, no evidence after that yet.
What's cool about them is that they were made and sold as an advertising novelty and a real jack at the same time. Everything from the "Jack-in-the-Box" name to the ad copy makes that very clear. They go out of their way to stress its utility, listing a number of uses, but make no bones about it being a "reproduction of the larger Simplex Screw Jacks" and state that its purpose is "to demonstrate and advertise the safety feature and power" of the larger jacks. "For the Home, Work Shop, Manual Training or a Xmas Gift." Shiftless's box, where the image of the jack is marked "A Simplex Souvenir", helps confirm that, too.
I think mine may be newer with the red paint.
It may be newer, but I wouldn't be too hasty to make that determination only on the color of that finish. The ads instruct buyers to pick between "red, blue or green Duco" initially (at least through 1931), and it was the orange that was added later. The only ad I can find that offers them in orange is 1935.
Here are some examples from 1927, 1929, 1930 and 1935.
Note the 1935 ad clearly confirming my World's Fair "sensation" souvenir.



